Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Arachidonic acid-hyaluronic acid conjugate as well as preparation method and application thereof

A technology of arachidonic acid and hyaluronic acid, which is applied in the directions of drug combination, pharmaceutical formulation, and inactive medical preparations, etc., to achieve the effects of improving bioavailability and safety, promoting apoptosis, and inhibiting migration and invasion.

Pending Publication Date: 2022-04-19
HENAN UNIVERSITY
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although traditional treatment methods have had little effect, with the rise of nanomedicine, the use of nanomaterials for targeted delivery of drugs has brought new solutions to the treatment of liver cancer

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Arachidonic acid-hyaluronic acid conjugate as well as preparation method and application thereof
  • Arachidonic acid-hyaluronic acid conjugate as well as preparation method and application thereof
  • Arachidonic acid-hyaluronic acid conjugate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation method of hyaluronic acid-eicosapentaenoic acid (HA-EPA) of the present embodiment, its synthetic route is as follows figure 1 As shown, the specific steps are as follows:

[0040] Synthesis of Hyaluronic Acid-Amine (HA-cys-amine)

[0041] Accurately weigh 20 mmol sodium hyaluronate and dissolve in deionized water, add 1.2 equivalents of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl), 3 equivalents Cystamine dihydrochloride and 2 M HCl were used to adjust the pH to 4.75. After stirring at room temperature for 2 h, 1 N NaOH was added to adjust the pH to 7 to terminate the reaction. The reaction solution was placed in a 8000 Da dialysis bag, dialyzed against deionized water for 48 h, and the dialysis water was changed every 4 h. After dialysis, the liquid was freeze-dried for 24 hours to obtain a milky white fluffy solid.

[0042] Synthesis of Eicosapentaenoic Acid Succinate Monoester Activator (EPA-NHS)

[0043] Dissolve 0.5 mmol...

Embodiment 2

[0047] The preparation method of hyaluronic acid-eicosapentaenoic acid (HA-EPA) of the present embodiment, its synthetic route is as follows figure 1 As shown, the specific steps are as follows:

[0048] Synthesis of Hyaluronic Acid-Amine (HA-cys-amine)

[0049] Accurately weigh 20 mmol sodium hyaluronate and dissolve it in deionized water, add 5 equivalents of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl), 5 equivalents successively Cystamine dihydrochloride and 2 M HCl were used to adjust the pH to 4.75. After stirring at room temperature for 2 h, 1 N NaOH was added to adjust the pH to 7 to terminate the reaction. The reaction solution was placed in a 8000 Da dialysis bag, dialyzed against deionized water for 48 h, and the dialysis water was changed every 4 h. After dialysis, the liquid was freeze-dried for 24 hours to obtain a milky white fluffy solid.

[0050] Synthesis of Eicosapentaenoic Acid Succinate Monoester Activator (EPA-NHS)

[0051] Dis...

Embodiment 3

[0055] The preparation method of hyaluronic acid-eicosapentaenoic acid (HA-EPA) of the present embodiment, its synthetic route is as follows figure 1 As shown, the specific steps are as follows:

[0056] Synthesis of Hyaluronic Acid-Amine (HA-cys-amine)

[0057] Accurately weigh 20 mmol sodium hyaluronate and dissolve in deionized water, add 0.5 equivalent of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl), 1 equivalent Cystamine dihydrochloride and 2 M HCl were used to adjust the pH to 4.75. After stirring at room temperature for 2 h, 1 N NaOH was added to adjust the pH to 7 to terminate the reaction. The reaction solution was placed in a 8000 Da dialysis bag, dialyzed against deionized water for 48 h, and the dialysis water was changed every 4 h. After dialysis, the liquid was freeze-dried for 24 hours to obtain a milky white fluffy solid.

[0058] Synthesis of Eicosapentaenoic Acid Succinate Monoester Activator (EPA-NHS)

[0059] Dissolve 0.5 mmol E...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of biological pharmacy, relates to preparation of anti-cancer drugs, and in particular relates to an arachidonic acid-hyaluronic acid conjugate as well as a preparation method and application thereof. The hyaluronic acid-arachidonic acid nanoparticle (HA-EPA) is synthesized, the chemical grafting rate of the EPA is about 40 + / -5% through nuclear magnetic detection, and the drug loading capacity is about 24 + / -3% through calculation; the infrared absorption spectrum confirms the synthesis of the hyaluronic acid-arachidonic acid graft; the measured particle size is 162.5 + / -10.2 nm, and the potential is 4.47 + / -0.31 mV; results show that the grafting of hyaluronic acid increases the toxicity of EPA on liver cancer cells HepG2 and Huh-7 and weakens the influence of EPA on normal liver cells LX-2, and HA-EPA can significantly inhibit the proliferation of HepG2 cells, promote the apoptosis of HepG2 cells and inhibit the migration and invasion of HepG2 cells (P is less than 0.001).

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals and relates to the preparation of anticancer drugs, in particular to an arachidonic acid-hyaluronic acid conjugate and its preparation method and application. Background technique [0002] Unsaturated fatty acids are a kind of fatty acids necessary for human growth and development. According to the chain length and degree of unsaturation, they are divided into monounsaturated fatty acids and polyunsaturated fatty acids. Eating polyunsaturated fatty acids can prevent or slow down the onset of disease. Studies have shown that EPA and DHA can increase the sensitivity of tumors to radiotherapy and reduce the mucosal and epithelial damage caused by radiotherapy. In vivo experiments also confirmed that omega-3 polyunsaturated fatty acids have more significant tumor suppressing advantages than omega-6 polyunsaturated fatty acids. Omega-3 polyunsaturated fatty acids can produce synergistic effects with...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): A61K47/61A61K31/202A61K31/728A61P35/00C08B37/08
CPCA61K47/61A61K31/202A61K31/728A61P35/00C08B37/0072A61K2300/00
Inventor 段少峰岑娟崔杰夏一帆白银都
Owner HENAN UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com